US8710244B2 - Dyes and methods of marking biological material - Google Patents
Dyes and methods of marking biological material Download PDFInfo
- Publication number
- US8710244B2 US8710244B2 US13/728,859 US201213728859A US8710244B2 US 8710244 B2 US8710244 B2 US 8710244B2 US 201213728859 A US201213728859 A US 201213728859A US 8710244 B2 US8710244 B2 US 8710244B2
- Authority
- US
- United States
- Prior art keywords
- dye
- biological material
- independently selected
- chemical formula
- mixtures
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 0 [1*]C1=C([1*])C2=C(C3=C([1*])C([1*])=C([2*]N4C(=O)C([1*])C([1*])C4=O)C([1*])=C3C(=O)[O-])C3=C([1*])C([1*])=C(C)C([1*])=C3OC2=C([1*])C1=C.[1*]C1=C([1*])C2=C(C3=C([1*])C([2*]N4C(=O)C([1*])C([1*])C4=O)=C([1*])C([1*])=C3C(=O)[O-])C3=C([1*])C([1*])=C(C)C([1*])=C3OC2=C([1*])C1=C Chemical compound [1*]C1=C([1*])C2=C(C3=C([1*])C([1*])=C([2*]N4C(=O)C([1*])C([1*])C4=O)C([1*])=C3C(=O)[O-])C3=C([1*])C([1*])=C(C)C([1*])=C3OC2=C([1*])C1=C.[1*]C1=C([1*])C2=C(C3=C([1*])C([2*]N4C(=O)C([1*])C([1*])C4=O)=C([1*])C([1*])=C3C(=O)[O-])C3=C([1*])C([1*])=C(C)C([1*])=C3OC2=C([1*])C1=C 0.000 description 12
- VVKSREKDGWPBHN-UHFFFAOYSA-N COC(=O)CNC(C)=O.COC(C)=O Chemical compound COC(=O)CNC(C)=O.COC(C)=O VVKSREKDGWPBHN-UHFFFAOYSA-N 0.000 description 4
- KGBVPPPURIQXEY-UHFFFAOYSA-N *.B.CC1=CC=C(S(=O)(=O)OC2=CC(N(CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)=CC=C2)C=C1.CC1=CC=C(S(=O)(=O)OC2=CC(N)=CC=C2)C=C1.O=S1(=O)CCCCO1 Chemical compound *.B.CC1=CC=C(S(=O)(=O)OC2=CC(N(CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)=CC=C2)C=C1.CC1=CC=C(S(=O)(=O)OC2=CC(N)=CC=C2)C=C1.O=S1(=O)CCCCO1 KGBVPPPURIQXEY-UHFFFAOYSA-N 0.000 description 1
- MFDADYKDPGENLN-UHFFFAOYSA-M B.C.CC1=CC=C(S(=O)(=O)OC2=CC(N(CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)=CC=C2)C=C1.O=S(=O)(O)CCCCN(CCCCS(=O)(=O)O)C1=CC=CC(O)=C1.[Li]O Chemical compound B.C.CC1=CC=C(S(=O)(=O)OC2=CC(N(CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)=CC=C2)C=C1.O=S(=O)(O)CCCCN(CCCCS(=O)(=O)O)C1=CC=CC(O)=C1.[Li]O MFDADYKDPGENLN-UHFFFAOYSA-M 0.000 description 1
- FEZZMNNGDRTISB-UHFFFAOYSA-N C.C.CC1=CC=C(S(=O)(=O)O)C=C1.O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=COC1=CC2=C(C=C1)C(=O)OC2=O.O=S(=O)(O)CCCCN(CCCCS(=O)(=O)O)C1=CC=CC(O)=C1 Chemical compound C.C.CC1=CC=C(S(=O)(=O)O)C=C1.O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=COC1=CC2=C(C=C1)C(=O)OC2=O.O=S(=O)(O)CCCCN(CCCCS(=O)(=O)O)C1=CC=CC(O)=C1 FEZZMNNGDRTISB-UHFFFAOYSA-N 0.000 description 1
- RYOVMDIKUGCYRU-UHFFFAOYSA-N C.CC1=CC=C(S(=O)(=O)O)C=C1.O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCS(=O)(=O)O)CCCS(=O)(=O)O)C=C2OC2=CC(C(CCS(=O)(=O)O)NCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCS(=O)(=O)O)CCCS(=O)(=O)O)C=C2OC2=CC(C(CCS(=O)(=O)O)NCCCS(=O)(=O)O)=CC=C21.O=COC1=CC2=C(C=C1)C(=O)OC2=O.O=S(=O)(O)CCCN(CCCS(=O)(=O)O)C1=CC=CC(O)=C1 Chemical compound C.CC1=CC=C(S(=O)(=O)O)C=C1.O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCS(=O)(=O)O)CCCS(=O)(=O)O)C=C2OC2=CC(C(CCS(=O)(=O)O)NCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCS(=O)(=O)O)CCCS(=O)(=O)O)C=C2OC2=CC(C(CCS(=O)(=O)O)NCCCS(=O)(=O)O)=CC=C21.O=COC1=CC2=C(C=C1)C(=O)OC2=O.O=S(=O)(O)CCCN(CCCS(=O)(=O)O)C1=CC=CC(O)=C1 RYOVMDIKUGCYRU-UHFFFAOYSA-N 0.000 description 1
- PHUKOMPKHVRRPE-UHFFFAOYSA-L C=C1C=CC2=C(C3=CC(C(=O)NCCCCCCC(=O)ON4C(=O)CCC4=O)=CC=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1.C=C1C=CC2=C(C3=CC=C(C(=O)NCCCCCCC(=O)ON4C(=O)CCC4=O)C=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1 Chemical compound C=C1C=CC2=C(C3=CC(C(=O)NCCCCCCC(=O)ON4C(=O)CCC4=O)=CC=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1.C=C1C=CC2=C(C3=CC=C(C(=O)NCCCCCCC(=O)ON4C(=O)CCC4=O)C=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1 PHUKOMPKHVRRPE-UHFFFAOYSA-L 0.000 description 1
- ODCPGYMPCOXZLQ-UHFFFAOYSA-L C=C1C=CC2=C(C3=CC(C(=O)ON4C(=O)CCC4=O)=CC=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1.C=C1C=CC2=C(C3=CC=C(C(=O)ON4C(=O)CCC4=O)C=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1 Chemical compound C=C1C=CC2=C(C3=CC(C(=O)ON4C(=O)CCC4=O)=CC=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1.C=C1C=CC2=C(C3=CC=C(C(=O)ON4C(=O)CCC4=O)C=C3C(=O)[O-])C3=CC=C(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)C=C3OC2=C1 ODCPGYMPCOXZLQ-UHFFFAOYSA-L 0.000 description 1
- JHTMRRLOFHSZGU-UHFFFAOYSA-N NCCCCCCC(=O)O.O=C(CCCCCCNC(=O)C1=CC=C(C(=O)[O-])C(C2=C3C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C3OC3=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C32)=C1)ON1C(=O)CCC1=O.O=C(CCCCCCNC(=O)C1=CC=C(C2=C3C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C3OC3=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C32)C(C(=O)[O-])=C1)ON1C(=O)CCC1=O.O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C1CCC(=O)N1O Chemical compound NCCCCCCC(=O)O.O=C(CCCCCCNC(=O)C1=CC=C(C(=O)[O-])C(C2=C3C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C3OC3=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C32)=C1)ON1C(=O)CCC1=O.O=C(CCCCCCNC(=O)C1=CC=C(C2=C3C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C3OC3=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C32)C(C(=O)[O-])=C1)ON1C(=O)CCC1=O.O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C1CCC(=O)N1O JHTMRRLOFHSZGU-UHFFFAOYSA-N 0.000 description 1
- FNLUTPXRIBDQMQ-UHFFFAOYSA-N O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC(C(=O)ON2C(=O)CCC2=O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)ON2C(=O)CCC2=O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C1CCC(=O)N1O Chemical compound O=C([O-])C1=CC(C(=O)O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC(C(=O)ON2C(=O)CCC2=O)=CC=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C([O-])C1=CC=C(C(=O)ON2C(=O)CCC2=O)C=C1C1=C2C=CC(=[N+](CCCCS(=O)(=O)O)CCCCS(=O)(=O)O)C=C2OC2=CC(C(CCCS(=O)(=O)O)NCCCCS(=O)(=O)O)=CC=C21.O=C1CCC(=O)N1O FNLUTPXRIBDQMQ-UHFFFAOYSA-N 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N O=S1(OCCCC1)=O Chemical compound O=S1(OCCCC1)=O MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Biotechnology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW101122353A TWI468469B (zh) | 2012-06-22 | 2012-06-22 | 染料與標記生物材料的方法 |
TW101122353 | 2012-06-22 | ||
TW101122353A | 2012-06-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
US20130344499A1 US20130344499A1 (en) | 2013-12-26 |
US8710244B2 true US8710244B2 (en) | 2014-04-29 |
Family
ID=49774742
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/728,859 Active US8710244B2 (en) | 2012-06-22 | 2012-12-27 | Dyes and methods of marking biological material |
Country Status (3)
Country | Link |
---|---|
US (1) | US8710244B2 (zh) |
CN (1) | CN103509366B (zh) |
TW (1) | TWI468469B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE49362E1 (en) | 2006-05-18 | 2023-01-10 | Illumina Cambridge Limited | Dye compounds and the use of their labelled conjugates |
WO2019068804A1 (fr) * | 2017-10-04 | 2019-04-11 | Unisensor | Dispositif de lecture optique à la carte d'un support solide amovible pour la détection et/ou la quantification d'analytes présents dans un échantillon |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6130101A (en) * | 1997-09-23 | 2000-10-10 | Molecular Probes, Inc. | Sulfonated xanthene derivatives |
US6383749B2 (en) | 1999-12-02 | 2002-05-07 | Clontech Laboratories, Inc. | Methods of labeling nucleic acids for use in array based hybridization assays |
US6448407B1 (en) | 2000-11-01 | 2002-09-10 | Pe Corporation (Ny) | Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis |
US6750357B1 (en) * | 1999-06-25 | 2004-06-15 | Syngen, Inc. | Rhodamine-based fluorophores useful as labeling reagents |
EP2036897A1 (en) | 2007-09-04 | 2009-03-18 | Roche Diagnostics GmbH | Stable rhodamine labeling reagent |
US20100197030A1 (en) | 2009-02-03 | 2010-08-05 | Biotium, Inc. | Xanthene dyes comprising a sulfonamide group |
US20100209354A1 (en) | 2007-10-01 | 2010-08-19 | Centre National De La Recherche Scientifique - Cnrs | Organic/inorganic hybrid nanoparticulates made from iron carboxylates |
US20100226991A1 (en) | 2007-10-01 | 2010-09-09 | Centre National De La Recherche Scientifique - Cnrs- | Solid inorganic/organic hybrid with modified surface |
WO2011029459A1 (en) | 2009-09-10 | 2011-03-17 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Novel photoactivable fluorescent dyes for optical microscopy and image techniques |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6323337B1 (en) * | 2000-05-12 | 2001-11-27 | Molecular Probes, Inc. | Quenching oligonucleotides |
-
2012
- 2012-06-22 TW TW101122353A patent/TWI468469B/zh active
- 2012-12-27 US US13/728,859 patent/US8710244B2/en active Active
-
2013
- 2013-03-07 CN CN201310073761.5A patent/CN103509366B/zh active Active
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6130101A (en) * | 1997-09-23 | 2000-10-10 | Molecular Probes, Inc. | Sulfonated xanthene derivatives |
US6750357B1 (en) * | 1999-06-25 | 2004-06-15 | Syngen, Inc. | Rhodamine-based fluorophores useful as labeling reagents |
US6383749B2 (en) | 1999-12-02 | 2002-05-07 | Clontech Laboratories, Inc. | Methods of labeling nucleic acids for use in array based hybridization assays |
US20060188915A1 (en) | 2000-11-01 | 2006-08-24 | Applera Corporation | Atropisomers of asymmetric xanthene fluorescent dyes and methods of dna sequencing and fragment analysis |
US6649769B2 (en) | 2000-11-01 | 2003-11-18 | Applera Corporation | Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis |
US7038063B2 (en) | 2000-11-01 | 2006-05-02 | Applera Corporation | Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis |
US6448407B1 (en) | 2000-11-01 | 2002-09-10 | Pe Corporation (Ny) | Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis |
US20070254298A1 (en) | 2000-11-01 | 2007-11-01 | Applera Corporation, Applied Biosystems Group | Atropisomers of asymmetric xanthene fluorescent dyes and method of dna sequencing and fragment analysis |
EP2036897A1 (en) | 2007-09-04 | 2009-03-18 | Roche Diagnostics GmbH | Stable rhodamine labeling reagent |
US20100209354A1 (en) | 2007-10-01 | 2010-08-19 | Centre National De La Recherche Scientifique - Cnrs | Organic/inorganic hybrid nanoparticulates made from iron carboxylates |
US20100226991A1 (en) | 2007-10-01 | 2010-09-09 | Centre National De La Recherche Scientifique - Cnrs- | Solid inorganic/organic hybrid with modified surface |
US20100197030A1 (en) | 2009-02-03 | 2010-08-05 | Biotium, Inc. | Xanthene dyes comprising a sulfonamide group |
WO2011029459A1 (en) | 2009-09-10 | 2011-03-17 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Novel photoactivable fluorescent dyes for optical microscopy and image techniques |
Non-Patent Citations (5)
Title |
---|
Boyarskiy et al., "Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment", Chemistry a European Journal, 2008, 14, pp. 1784-1792. |
Liu et al., "Rational design and synthesis of a novel class of highly fluorescent rhodamine dyes that have strong absorption at long wavelengths", Tetrahedron Letters, 2003, 44, pp. 4355-4359. |
Meng et al., "Synthesis of N-hydroxysuccinimidyl benzoate and its structural insight into labeling activity of fluorescent probes", Dyes and Pigments, 2007, 75, pp. 166-169. |
Mujumdar et al., "Cyanine Dye Labeling Reagents Containing Isothiocyanate Groups", Cytometry, 1989, 10, pp. 11-19. |
Shandura et al., "New heterocyclic analogues of rhodamines", Dyes and Pigments, 2007, 73, pp. 25-30. |
Also Published As
Publication number | Publication date |
---|---|
US20130344499A1 (en) | 2013-12-26 |
TWI468469B (zh) | 2015-01-11 |
CN103509366B (zh) | 2015-09-30 |
TW201400551A (zh) | 2014-01-01 |
CN103509366A (zh) | 2014-01-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107235946A (zh) | 一种谷胱甘肽荧光探针及其制备方法和应用 | |
JP5070057B2 (ja) | 新規な蛍光標識化合物 | |
US20080108141A1 (en) | Diaminorhodamine derivative | |
US8101655B2 (en) | Fluorescent dyes and complexes | |
WO2020033173A1 (en) | Polymeric tandem dyes having pendant narrow emission acceptor | |
JP7344982B2 (ja) | 化合物及びこれを用いた蛍光標識生体物質 | |
CN107445949B (zh) | 荧光化合物及其制造方法 | |
US20120095187A1 (en) | Novel cyanine compound for labeling biomolecule and preparation method thereof | |
US20210395606A1 (en) | Chromophoric structures for macrocyclic lanthanide chelates | |
US8710244B2 (en) | Dyes and methods of marking biological material | |
US8063200B2 (en) | Labeled compound and detection method using the same | |
KR101663465B1 (ko) | 생체 분자 표지를 위한 시아닌 염료 및 그 제조방법 | |
CN110357817B (zh) | 一类可逆性检测丙酮醛和乙二醛荧光探针及其制备方法和应用 | |
US8927672B2 (en) | Benzindocyanine compound for labeling substance, intermediate thereof, and method for preparing the same | |
US20100029017A1 (en) | Mono-chlorinated hydroxycoumarin conjugates | |
JP6596733B2 (ja) | 化合物、該化合物を含有するタンパク質修飾試薬およびタンパク質の標識方法 | |
KR101125058B1 (ko) | 물질 표지용 화합물 및 그 제조방법 | |
US20230098702A1 (en) | Amphoteric fluorescent substance capable of being attached to biomaterials | |
US5151517A (en) | Derivatives of tetrahydro-2,3,6,7,1h,5h,11h-(1)benzopyrano(6,7,8,i,j)quinolizinone-11 usable as markers for organic compounds, particularly biological compounds with a view to their detection by chemiluminescence or fluorescence | |
KR102260233B1 (ko) | 메로시아닌계 화합물, 이를 포함하는 생체분자 표지용 염료, 키트 및 조영제 조성물 | |
US20240165240A1 (en) | Compound and labeled biological substance using the same | |
US20240173437A1 (en) | Compound and labeled biological substance using the same | |
US20200247831A1 (en) | Amino-sila-pyronin compound-based one- or two-photon absorption fluorescent substance and use thereof | |
WO2022191123A1 (ja) | 蛍光性化合物及びこれを用いた蛍光標識生体物質 | |
US20240182383A1 (en) | Compound and labeled biological substance using the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE, TAIWAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:WANG, SHIN-SHIN;REEL/FRAME:029543/0727 Effective date: 20121213 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551) Year of fee payment: 4 |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 8TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1552); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 8 |